benzyl oleanolate 3-O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-α-L-arabinopyranoside | 1355346-19-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: benzyl oleanolate 3-O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-α-L-arabinopyranoside
• 英文别名: benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-α-L-arabinopyranoside；benzyl (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[[(3aS,6S,7R,7aS)-2,2-dimethyl-7-[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 1355346-19-8
• 化学式: C₅₇H₈₂O₁₄
• 分子量: 991.27
• InChiKey: VDHVVJHIHCFXRL-UJELCQBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  71
• 可旋转键数：
  14
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  161
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  benzyl oleanolate 3-O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-α-L-arabinopyranoside 在 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 benzyl oleanolate 3-O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)-4-O-acetyl-α-L-arabinopyranoside
  参考文献：
  名称：

  Facile Synthesis of the Naturally Cytotoxic Triterpenoid Saponin Patrinia-Glycoside B-II and Its Conformer

  摘要：

  首次以线性 11 步序列 11 完成了天然三萜皂苷 Patrinia-glycoside B-II 即齐墩果酸 3-O-α-L-rhamnopyranosyl-(1→2)-[β-D-Gluco-pyranosyl-(1→3)]-α-L-arabinopyranoside 的化学合成，总收率为 9.4%。研究发现，阿拉伯糖残基的异常 1C4 构象是在制备中间体的过程中通过构象波动产生的。分子机理和量子化学计算表明，在正常条件下，帕特里尼亚糖苷 B-II 及其构象 1 不能相互转化。初步的结构-活性关系研究表明，独特的α-L-吡喃鼠李糖基-(1→2)-α-L-阿拉伯吡喃糖基二糖分子中阿拉伯糖残基的 4C1 椅构象是其对肿瘤具有细胞毒性活性的主要积极因素之一。

  DOI：

  10.3390/molecules181215193
• 作为产物：
  描述：

  2,3,4-tri-O-benzoyl-β-L-arabinopyranosyl trichloroacetimidate-⁴C₁ 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 9.0h， 生成 benzyl oleanolate 3-O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-α-L-arabinopyranoside
  参考文献：
  名称：

  Facile Synthesis of the Naturally Cytotoxic Triterpenoid Saponin Patrinia-Glycoside B-II and Its Conformer

  摘要：

  首次以线性 11 步序列 11 完成了天然三萜皂苷 Patrinia-glycoside B-II 即齐墩果酸 3-O-α-L-rhamnopyranosyl-(1→2)-[β-D-Gluco-pyranosyl-(1→3)]-α-L-arabinopyranoside 的化学合成，总收率为 9.4%。研究发现，阿拉伯糖残基的异常 1C4 构象是在制备中间体的过程中通过构象波动产生的。分子机理和量子化学计算表明，在正常条件下，帕特里尼亚糖苷 B-II 及其构象 1 不能相互转化。初步的结构-活性关系研究表明，独特的α-L-吡喃鼠李糖基-(1→2)-α-L-阿拉伯吡喃糖基二糖分子中阿拉伯糖残基的 4C1 椅构象是其对肿瘤具有细胞毒性活性的主要积极因素之一。

  DOI：

  10.3390/molecules181215193

文献信息

• Synthesis, biological evaluation and structure-activity relationship studies of hederacolchiside E and its derivatives as potential anti-Alzheimer agents
  作者：Hui-ning Li、Yang Liu、Zuo-peng Zhang、Zhi-peng Wang、Jing-zheng Hao、Feng-ran Li、Zhan-fang Fan、Li-bo Zou、Mao-sheng Cheng

  DOI：10.1016/j.ejmech.2017.11.040

  日期：2018.1

  Inspired by the previously reported neuroprotective activity of hederacolchiside E (1), we synthesized hederacolchiside E for the first time along with eleven of its derivatives. The neuroprotective effects of these compounds were further evaluated against H2O2- and A beta(1-42)-induced injury using cell-based assays. The derivatives showed obvious differences in activity due to structural variations, and two of them exhibited better neuroprotective effects than 1 in the A beta(1-42)-induced injury model. Compound 7 was the most active derivative and had a relatively simple chemical structure. Moreover, 1 and 7 can significantly reduce the release of lactate dehydrogenase (LDH), level of intracellular reactive oxygen species (ROS) and extent of malondialdehyde (MDA) increase resulting from A beta(1-42) treatment, which demonstrated that these kinds of compounds show neuroprotective effects in Alzheimer's disease (AD) models via modulating oxidative stress. Compound 7 could be used as promising lead for the development of a new type of neuroprotective agent against AD. (C) 2017 Elsevier Masson SAS. All rights reserved.